The 25 best movies set in Chicago

This is perhaps the quintessential Chicago film. Jake and Elwood Blues are Chicago boys through and through. The streets of the city are all over the movie, thanks to car chases (and car crashes) that fill the film. The Blues Brothers is full of famous musicians and most every famous Chicago spot of the time.

Look, it’s the Best Picture winner that’s literally just called Chicago. We had to include it. While this musical has perhaps not stood the test of time, it was a huge hit and served a stylish representation of the Windy City in a different era.

Granted, a lot of the action in Airplane! takes place on an airplane. However, that plane is flying from Los Angeles to Chicago. All of those guys in the control tower, like Lloyd Bridges and Robert Stack? They are all in Chicago. This is undoubtedly one of the best Chicago movies.

The 1919 Chicago White Sox is one of the most infamous teams in sports history. Known as the Black Sox, the team threw the World Series that year, leading to eight members of the team being banned from baseball for life. That includes the famous “Shoeless” Joe Jackson. Eight Men Out is the story of that team.

Back-to-back baseball films! Hey, Chicago has two MLB clubs, including the Cubbies, so it only makes sense. There aren’t any men playing baseball in A League of Their Own, though. This film is about a women’s baseball league that started up during World War II. There is no crying in baseball, but there are laughs in this movie.

This is one of the movies that needed deliberation, but we came down on the side of it being a Chicago movie. Chicago is the most important city in the movie, even if Robert De Niro’s Jack Walsh is taking Charles Grodin’s bail skipper Johnathan “The Duke” Mardukas from New York to LA. They both have Chicago ties, with Jack being a former Chicago cop and “The Duke” being the accountant for a Chicago mob boss. For a section of the film, they stop in Chi-town, and this is a great movie, so we wanted to include it.

Another Best Picture winner, though perhaps less immediately affiliated with Chicago. It’s not literally called Chicago, after all. This grim family drama won Best Picture in 1980, famously beating Raging Bull. It gives you a whole different view of Mary Tyler Moore, and Timothy Hutton won an Oscar in his film debut.

Hey, another Best Picture winner! And who says Chicago is the Second City? Now, this is a throwback version of Chicago. There’s no Willis Tower or that giant metal bean. But there is flim-flam and con artistry. This is a movie about two hucksters pulling off a long con on a Chicago mob boss. Apparently, Chicago is the city of Best Picture winners and mobsters.

Michael Mann loves Chicago. This, his feature-film debut, is his most Chicago movie. It’s lean, gritty, and bleak. James Caan stars in a crime film even less romanticized than The Godfather. Mann isn’t fully fleshed out as a filmmaker, but it’s a strong introduction to his style.

Obviously, we could have also included Wayne’s World 2, which takes place in Chicago. Or, should we say, the Chicago suburb of Aurora. It’s very much a Chicago movie, though. They hang out at Stan Mikita’s Donuts! This is totally a Chicago movie! Way!

In a way, Mean Girls could have taken place anywhere. It’s mostly about the environs of a high school. People can wear pink on Wednesday from coast to coast. That being said, this beloved 2000s comedy happens to take place in Evanston, another suburb of Chicago. We wouldn’t think about leaving it off this list.

John Hughes loved setting movies in Chicago. We wanted only to choose one to represent them all. Ferris Bueller’s Day Off has the most Chicago feel to it, but Ferris is a creep, and we don’t need to boost his ego any further. As such, we decided to go with The Breakfast Club, even if it takes place almost entirely within a school library.

Chucky has been having a bit of a comeback, but let’s go to the very beginning. While the Child’s Play series would become much more meta and delve into the world of horror-comedy, the first film in the series is just a straight-up horror flick about a doll possessed by the spirit of a serial killer. All the action takes place in Chicago, and the city gets plenty of shine, including a trip on the “El” train.

In terms of trips through the streets of Chicago, The Fugitive is right up there with The Blues Brothers. Based on an old TV series, the story follows Dr. Richard Kimble as he searches for the one-armed man who killed his wife. During one part of the movie, he sneaks into the St. Patrick’s Day parade to hide, which is very much a Chicago thing.

Nick Hornby’s book about a list-loving record store owner is set in London, which is fitting because he’s an Englishman. The movie stars John Cusack, though, and Cusack is a Chicago boy. As such, the action of the High Fidelity film takes place in the Windy City, which probably gave the story a boost in quality.

While this film is perhaps not remembered as a classic, Otto Preminger’s movie was important. It helped to break down the Production Code in Hollywood with its language and depictions of drug use. Frank Sinatra stars in the sort of stripped-down drama stars like to make to show they are more than their image. He plays a Chicago native released from prison for drug possession and trying to avoid relapsing into heroin use.

This is a fresh addition to the list but a worthy one. Daniel Kaluuya won an Oscar for playing Fred Hampton in this story of the Black Panther leader in Chicago. Hampton’s story is an important, interesting, and ultimately sad one. This film is a worthy attempt to capture part of his life. Kaluuya is really good, though the fact that he and Lakeith Stanfield were nominated for Best Supporting Actor is a bit of category fraud.

This classic farce is only a Chicago movie for a while, but it begins as a Chicago film, and it’s a beloved comedy, so we are happy to include it. That’s especially because a famous Chicago event from real life is involved. Tony Curtis and Jack Lemmon play to Chicago musicians who see what is effectively a replication of the St. Valentine’s Day massacre and thus have to go on the run. Naturally, they dress as women to join an all-female band on tour. It’s funnier than it might sound.

Much like The Fugitive, The Untouchables is based on an old TV show. Well, in this case, it’s also based on reality. Brian De Palma’s movie tells the story of Elliot Ness and his men trying to take down Al Capone. Sean Connery won an Oscar. De Palma did an overwrought homage to Battleship Potemkin. That’s the Chicago way.

Crime and Chicago go hand in hand, at least in movies. To be fair, crime is a popular subject for movies. We don’t take it as a sign Chicago is nothing but a den of crime. Chicago politics plays a big role in Widows, to the degree that is particularly dense but appreciated. It’s also a heist film, in case Chicago politics don’t interest you.

The Griswolds are a Chicago family, but they are often on vacation. Either they are going to Vegas or Europe or Wally World. Christmas Vacation is about celebrating Christmas, which means settling in at home. Not that this movie is any less of a disaster for the Griswolds, though.

The Scarface people remember (the one with Al Pacino) is set in Miami. The film centers on Tony Montana, a Cuban immigrant. It’s a modernization of this Scarface, more directly inspired by Al Capone. This one stars Paul Muni as Tony Mendoza, an Italian immigrant who, like Capone, settles into Chicago.

Inside Llewyn Davis is a great New York movie and a good Chicago movie. Llewyn takes a trip to Chicago in the film to try and get his music career back on track. There’s a fabulous scene where he performs a song for F. Scott Abraham’s character, and that is in Chicago. It earned this movie a spot on the list.

My Big Fat Greek Wedding is a fascinating story. Nia Vardalos was adapting her play thanks to the help of Rita Wilson and Tom Hanks, who had seen and liked it. It cost all of $5 million. It made $368.7 million worldwide and $241.4 million in North America. It became the highest-grossing romantic comedy of all time, and until “Sing” had the highest box office of a film never to reach No. 1.

We’ve had plenty of looks at Chicago in the past. Here’s a look at Chicago in the future. OK, this is not a Chicago any of us are familiar with. None of us have joined Will Smith in this future where robots are sentient and maybe committing murder. Still, it’s a Chicago movie, and we wanted to include a sci-fi version of the Windy City for the list. I, Robot was the best choice.